It was the mixtape that launched a thousand memes: Young Thug’s Jeffrey, the cover art of which features the gangly, six-foot-three-inch rapper decked out in a dramatic gown of floor-sweeping periwinkle ruffles. Save for the tattoo art creeping up his bejeweled wrists and the twisted dreadlocks poking out from under his conical hat—like a cocktail umbrella, only gigantic—the hip-hop star is barely recognizable. Could this really be Jeffrey Lamar Williams, better known as Young Thug, or was this some aspiring performance artist scrambling for Internet fame?
The hip-hop Twitterverse for sure knew their guy. His flamboyant selfies were already the stuff of Instagram legend, brimming with pearl and diamond chokers, fur-trimmed Ugg boots, and colorful Fendi pom-pom keychains that swung from the belt loops of his skinny jeans. Within hours of its release on August 25, 2016, the image had spread across social media, igniting a debate that seemed to rage on for months thereafter: Here was a male rapper who dared to command the world of hip-hop, a genre so often defined by hypermasculinity, in a dress. Was the world ready?
Though the initial uproar surrounding the cover—much of it blatantly homophobic—threatened to overshadow its success, the mixtape was well-received by critics. In fact, the record would end up topping many of the most important end-of-year lists, including those of Rolling Stone and Pitchfork. Beyond the music, Thug had clearly touched a raw nerve in the culture with his radical gender-bending fashion statement. Granted, he wasn’t the first rapper from Atlanta to have experimented with gender-fluidity—André 3000 famously wore a long white shift dress on the cover art for the hit single, “Ms. Jackson,” over a decade earlier in 2000—but he was undoubtedly the first to do so in the era of trap music, the southern, street-smart sound that has come to dominate the 2010s. (Of course in the gay and trans underground, where rappers like Mykki Blanco expressed their gender and sexual orientation in all kinds of ways, this wasn’t news at all.)
Circa 2019 and with the emergence of Lil Uzi Vert, Playboy Carti, and Lil Nas X, it’s almost de rigueur for even rappers in the mainstream to flirt with gender norms. “Young Thug tiptoed this line between being macho, a man who grew up on the streets of Atlanta, and someone who wasn’t afraid to push this very androgynous look,” says Pitchfork’s Alphonse Pierre. “You could hear a vulnerability in his sound, if not in his lyrics—in the high pitch of his voice. There’s an airiness and a brightness to the production, too. He helped open up the space for a new generation of rappers who weren’t afraid to show a softer side.”
As someone who grew up listening to music that ran the gamut of Public Enemy and David Bowie, Thug was every bit the millennial space oddity that I had been waiting for. And as a fashion editor who had been reporting on the collections in New York and Europe for the better part of a decade, he was emblematic of a seismic shift that was afoot on the runways, too. The seemingly rigid line that had once divided menswear and womenswear was rapidly dissolving: Alessandro Michele had made his groundbreaking debut at Gucci a little over a year earlier and was dressing doe-eyed, long-haired male models in pussy-bow blouses and fanciful brocade; J.W. Anderson made tabloid headlines in the U.K. when he included dresses in his Fall 2013 menswear collection; and Jaden Smith had starred in Louis Vuitton’s women’s campaign wearing a skirt that same year. A little over six months after Jeffrey, Pharrell Williams would be the first man to star in a Chanel handbag campaign.
To fully understand how the stage was set for a style renegade like Thug, you kind of have to go back to the turn of the decade, to hip-hop’s most infamous fashion obsessive, Kanye West. Rappers have always had an appetite for luxury—in the ’90s, Biggie was known for his Versace habit—but few had truly courted the attention of designers in the way that West did. Though Cam’ron had made pink his religion in the early aughts, he still felt the need to qualify it with a “No Homo” every chance he got.
Captured by Tommy Ton back in 2009, the image of Kanye West and his entourage outside the Commes des Garçons Homme show in Paris stands as a pretty uncanny harbinger of things to come. West is pictured carrying a Goyard briefcase, dressed in a tailored plaid trench coat, fitted jeans, and red leather driving gloves; on his feet, the sleek Louis Vuitton sneakers he designed in collaboration with Marc Jacobs, then at the helm of the French house. At the rapper-producer’s side is Virgil Abloh, his friend and then little-known creative director. Like West, he’s wearing an outfit that is equal parts spiffy and streetwise: turquoise Moncler puffer vest, eye-catching red specs, and bright yellow sneakers. Who could have predicted that these two street style peacocks would rise to be major players in the fashion world?
At the time, West and his fashion cohorts were ridiculed by many of their music industry peers for their dandy fashion choices: the bright colors, the form-fitting silhouettes, the designer man bags. Back then, the look of hip-hop was generally defined by an oversize, low-slung silhouette, a swaggering sensibility that was echoed in the hypermasculine tone of the era. Before West’s impassioned 808s & Heartbreak was released in 2008, the early aughts were under the sway of gangsta rap with albums like 50 Cent’s Get Rich Or Die Tryin’ ruling the airwaves. Whatever his dubious rightwing politics might be now, West was seen as something of a thought leader in hip-hop back then. Where 50 Cent was openly spouting anti-gay rhetoric, West had apologized for his homophobic lyrics, encouraging support for LGBTQI+ rights instead.
In fashion terms, that which divided the old guard from the new came down the proportions of their pants. Danny Brown, an indie rapper from Detroit who gained popularity in the early 2010s, claimed to have been refused a record deal by 50 Cent based on the fact that Brown was wearing skinny jeans. Lil Wayne caused an online frenzy when he performed at the VMAs in 2011 dressed in women’s leopard-print jeggings. Though he’s considered an eccentric outlier of mainstream hip-hop, Lil B hit on the moment when he released “Tight Pants” in 2011, a single in defense of the slinky rock ’n’ roll look. Four years later, he caused a stir all over again, appearing on ESPN’s SportsNation wearing a sheer shirt, chandelier earrings, and a floppy hat. “People aren’t used to seeing something so different, a guy who is comfortable wearing women’s clothes,” says Lil B, speaking over the phone from his home in the Bay Area. “For me it comes from a really true place, it was about moving the culture forward, and letting the next generation know they could do this.”
Though West was not what you’d call androgynous, he clearly wasn’t averse to experimenting with womenswear. He took to the stage at Coachella in 2011 sporting a much-coveted Celine women’s blouse. Perhaps in homage to that forward-thinking style, Travis Scott posted an Instagram picture of himself last fall in the very same printed silk shirt. A few years after West’s controversial Coachella fashion moment, Kid Cudi, who was an early signee to West’s GOOD music label, would up the ante, appearing on stage at the festival in a crop top.
Over on the East Coast, meanwhile, A$AP Mob, a new collective of hip-hop style risk-takers led by a Rakim Myers, a handsome young rapper from Harlem who went by the name ASAP Rocky, was emerging. He had a knack for nailing tricky-to-pull-off runway looks, many of which challenged gender norms (man bags, pearls, etc.). In fact, few men (or women for that matter) can claim to rock a babushka with quite the same panache as he does. Those no-holds-barred fashion instincts earned Rocky a front row seat at just about every important men’s show in Paris and Milan. But more than that, it won him the respect of some of the most visionary designers of the decade: Rick Owens, Gucci’s Alessandro Michele, and most notably Raf Simons. Besides being a really great clotheshorse, Rocky was carving out space for a new kind of open-minded hip-hop renaissance man, one who was wasn’t confined to any one creative pursuit; rather, he dabbled in all of them—music, art, design, film, fashion. Suddenly the idea of drawing boundaries, be they along gender or genre lines, seemed deeply old-fashioned.
If there is one designer who fully comprehends the influence of the hip-hop multi-hyphenate, it’s Virgil Abloh. Beyond bringing out some of the biggest names in music—Rihanna, Travis Scott, and Kanye West, with whom he shared an emotional bear hug at his debut show for Louis Vuitton—the creative director has also collaborated with some of the most important new voices on the scene right now, none more weird, wonderful, or boundary-pushing than Lil Uzi Vert. Abloh created the cover art for Luv Is Rage 2 (2017), the rapper’s critically acclaimed debut album, plastering a black-and-white image of Uzi with his signature Off-White tape. Abloh also directed the video for “XO Tour Llif3,” the hit single that became an anthem for emo rap, the emotionally-charged genre of hip-hop popularized by Uzi and the late rapper Lil Peep. In the clip, Uzi is in his deepest, darkest feelings, staggering around the 10th arrondissement of Paris dressed in a crystal-studded black sweater, tight black pants, and a cropped hooded jacket replete with bondage-style straps. It’s by no means his most flamboyant fashion moment.
The self-proclaimed rockstar appeared at the Billboard Awards in 2017 wearing a sheer lace Valentino with frilly sleeves and shut down the red carpet. Then there was the time he inadvertently paid homage to Avril Lavigne on Instagram, dressed in a black and pink off-the-shoulder Faith Connexion top with a matching Goyard satchel bag. (The side-by-side meme of the two musicians went viral.) He’d already caused a sensation on social media with the $200,000 custom diamond pendant he had made in the image of his idol, Marilyn Manson.
Uzi’s ferocious shopping habit (Dover Street Market, Barneys, etc.) has since made his Instagram feed compulsive viewing. Meticulously curated, his fit pics are all hashtagged “No Stylist” to remind the world just how personal his fashion obsession is. His wardrobe is a veritable teenage girl fantasy, furnished with strawberry-print Gucci skinny jeans, JNCO-style raver pants, Hello Kitty beanie hats, and cutesy Mickey Mouse handbags. Drawing on this kooky mix of Harajuku, goth, and punk stylings, Uzi is like the brooding antihero in some futuristic manga movie. In his photos, the whites of his eyes often appear unusually wide, as if they’ve been brightened in Photoshop to accentuate this bizarre anime persona. In fact, if you had to place Uzi on the gender spectrum, you’d probably end up at cartoon.
There have been plenty of question marks around Uzi’s sexuality as a result of his rule-breaking style. Thankfully, the rapper seems refreshingly unfazed, posting his most life-affirming fit pic yet in June, posed against a rack of brightly colored tulle dresses with a rainbow flag across his chest in support of Pride. He’d for sure have no problem pulling off Abloh’s latest offering for Louis Vuitton. Awash with soft pink chiffon, sheer raincoats, and flower sprigged harnesses, it was undoubtedly Abloh’s most romantic collection yet, one that is also in line with the new, gentle mood of hip-hop right now. Tyler, the Creator’s Flower Boy, springs to mind—the album title is also the term used to describe delicate-looking, androgynous young men in Korea. The emotionally expressive nature of the SoCal rapper’s music is only amplified by his taste for pastel colors and the signature daisy prints that appear all over his Golf Wang clothing line.
Then there’s Lil Nas X, hip-hop’s favorite cowboy, whose genre-defying “Old Town Road” song topped the charts for 14 weeks this year. The 20-year-old openly gay artist reinvented the macho western look with a wardrobe that tends towards pretty sparkle and shine—think: a glittery purple shirt trimmed with fringe made from crystal beads, iridescent cowboy boots, and dangling earrings. In a recent podcast interview, Young Thug was asked to comment on Lil Nas X’s coming out. Rather surprisingly, his remarks were behind the times. “I feel like he probably shouldn’t have told the world, because these days motherfuckers is just all judgment.... It ain’t even about the music no more,” said Thug. “He’s young and backlash can come behind anything.”
As we approach 2020, perhaps the question isn’t whether the world is ready for a rapper in a dress, but rather one who wears his whole self on his sleeve.